EP0433070B1 - Fluorkohlenstoffhaltige Beschichtungszusammensetzung und daraus abgeleitete Produkte - Google Patents

Fluorkohlenstoffhaltige Beschichtungszusammensetzung und daraus abgeleitete Produkte Download PDF

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Publication number
EP0433070B1
EP0433070B1 EP90313595A EP90313595A EP0433070B1 EP 0433070 B1 EP0433070 B1 EP 0433070B1 EP 90313595 A EP90313595 A EP 90313595A EP 90313595 A EP90313595 A EP 90313595A EP 0433070 B1 EP0433070 B1 EP 0433070B1
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EP
European Patent Office
Prior art keywords
polyfluoropolyether
composition
weight
coating
release
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EP90313595A
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English (en)
French (fr)
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EP0433070A2 (de
EP0433070A3 (en
Inventor
Mark J. C/O Minnesota Mining And Pellerite
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3M Co
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Minnesota Mining and Manufacturing Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C09J7/401—Adhesives in the form of films or foils characterised by release liners characterised by the release coating composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/414—Additional features of adhesives in the form of films or foils characterized by the presence of essential components presence of a copolymer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2427/00—Presence of halogenated polymer
    • C09J2427/005—Presence of halogenated polymer in the release coating
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2471/00—Presence of polyether
    • C09J2471/005—Presence of polyether in the release coating
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/14—Layer or component removable to expose adhesive
    • Y10T428/1424—Halogen containing compound
    • Y10T428/1429—Fluorine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2839—Web or sheet containing structurally defined element or component and having an adhesive outermost layer with release or antistick coating
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848—Three or more layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852—Adhesive compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
    • Y10T428/31544—Addition polymer is perhalogenated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane

Definitions

  • This invention relates to release liners, and more particularly, to release liners suitable for use with highly aggressive pressure-sensitive adhesives.
  • Pressure-sensitive adhesive tape which is typically wound into rolls, has a low-adhesion backsize coating applied to the major surface of the backing not bearing adhesive to permit the tape to be unwound without delamination and transfer of adhesive to the surface of the backing not bearing adhesive.
  • the force required to separate the adhesive layer from the low-adhesion backsize coating i.e., peel force, ranges from 6 to 35 Newtons per decimeter (N/dm) per unit width.
  • the tape is not wound into a roll, its adhesive layer is customarily protected by a disposable web that bears a low-adhesion coating to which normally tacky and pressure-sensitive adhesives adhere very weakly, e.g., a peel force ranging from about 0.2 to about 6 N/dm, preferably 0.2 to 2 N/dm. Release coatings having peel forces in this preferred range of 0.2 to 2 N/dm are hereinafter referred to as "premium release" coatings.
  • Certain pressure-sensitive adhesives are so aggressive that tapes employing them exhibit undesirably high peel forces upon removal from known low-adhesion coatings, especially after prolonged storage or when used in a high-temperature environment.
  • the adhesive of such tapes may carry away, and consequently, be contaminated by appreciable amounts of the low-adhesion material. If this occurs, the tapes will exhibit poor readhesion when applied to "end-use" receptor surfaces.
  • Known low-adhesion coatings e.g., poly(urethanes), poly(tetrafluoroethylenes), and poly(dimethylsiloxanes), do not provide release peel forces in the range 0.2 to 2 N/dm when used with poly(dimethylsiloxane) adhesives.
  • U.S. Patent No. 4,321,404 describes abherent coatings made by using electron beam radiation to polymerize a mixture of film-forming and polyfluorinated oligomers in a single step. The mixture is formulated so that the fluorinated materials tend to segregate at the coating surface, i.e., the air interface, so that the abherent coating can be crosslinked with a single pass through the electron beam curtain. These coatings have excellent readhesion; however, they were formulated for use with acrylic adhesives and typically have high release values when used with these adhesives. These release values would be higher still if these abherent coatings were used with the highly aggressive silicone pressure-sensitive adhesives.
  • U.S. Patent Nos. 4,567,073 and 4,614,667 disclose the advantage of first photopolymerizing a thin layer of a film-forming polymer that is strongly bonded to the surface of a substrate.
  • This primer layer is also capable of subsequently reacting with functional groups attached to a polyfluoropolyether, which is applied as a second thin layer over the photopolymerized layer, thereby chemically bonding the release coating to the inner primer layer.
  • These release liners exhibit release of about 0.6 N/dm, and excellent readhesion for certain classes of silicone-based pressure-sensitive adhesives.
  • US-A-4 820 588 discloses polyfluoropolyether compositions that are inert liquids which can be used as hydraulic fluids and lubricants, and also functional polyfluoropolyether compositions comprising mono- and di-functional polyfluoropolyethers which are useful as lubricants, surface active agents, release agents for pressure-sensitive adhesives, etc.
  • the functional polyfluoropolyether compositions prepared are generally mixtures of monofunctional, difunctional, and inert compounds. Products called “monofunctional” generally contain less than 25 weight percent each of difunctional and inert compounds. Products called “difunctional” preferably contain less than 20, more preferably less than 10 weight percent total monofunctional and inert compounds.
  • the functional polyfluoropolyether compositions are used as a release coating, for example, for pressure-sensitive adhesive tape
  • a solution of the polyfluoropolyether composition preferably a composition having acrylate or methacrylate functionality
  • the substrate for example, a flexible film.
  • the coating is then dried and the polyfluoropolyether composition is polymerized to form a cohesive network adhered to the substrate.
  • An adhesive layer such as a poly(dimethylsiloxane) can then be releasably adhered to the polymerized polyfluoropolyether composition.
  • the present invention provides curable, crosslinkable compositions and coatings prepared therefrom that can be used to form low-surface energy liners that can be used with aggressive pressure-sensitive adhesives, such as adhesives formed from silicone resins.
  • aggressive pressure-sensitive adhesives such as adhesives formed from silicone resins.
  • the release characteristics of these coatings do not diminish upon aging and do not adversely affect the readhesion properties of adhesives that have come in contact with the coatings.
  • compositions of the present invention comprise a crosslinkable polyfluoropolyether and an inert polyfluoropolyether oil.
  • the compositions can be dissolved in mixtures of fluorinated solvents in order to provide solutions having a viscosity suitable for coating by methods well known in the art.
  • the composition preferably contains from 15 to 75% by weight crosslinkable polyfluoropolyether, more preferably from 50 to 75% by weight, and from 25 to 85% by weight inert polyfluoropolyether oil. It is preferred that the polyfluoropolyether oil have a viscosity of 20 to 500 centipoise at 25°C, more preferably 90 to 200 centipoise at 25°C.
  • the invention further provides substrates bearing a layer of the composition of the invention.
  • These coated substrates are particularly suitable for release liners, especially differential release liners and low-adhesion backsizes for pressure sensitive adhesive tapes and sheet materials, especially for pressure-sensitive adhesives derived from silicone resins.
  • release coatings of this invention are specifically formulated and cured to resist cohesive failure within the bulk phase but to fail uniformly along an extremely thin, weak boundary layer at the release coating-adhesive interface.
  • silicone adhesives on the fluorochemical release liners of the present invention will not suffer dramatic reductions of the readhesion value, as will acrylic adhesives on silicone-based release liners if uncured material is present.
  • pressure-sensitive adhesives in contact with the release liners of the present invention can have very high readhesion values--in excess of 90% of those of control adhesives which have not been in contact with any release coating or liner. Such high readhesion values are indicative of little, if any, transfer of fluorocarbon materials of low surface energy to the pressure-sensitive adhesive.
  • the coatings of this invention can have more than 50% by weight inert oils without significantly reducing the readhesion of adhesives removed from them, they provide an economic advantage over those coatings prepared by using only the more expensive reactive group-containing polyfluoropolyethers.
  • polyfluoropolyether polymers having non-perfluorinated, crosslinkable end groups such as acrylate, isocyanato, or bis(amidopropyltriethoxysilane).
  • crosslinkable end groups such as acrylate, isocyanato, or bis(amidopropyltriethoxysilane).
  • inert polyfluoropolyether fluids useful in the practice of this invention include those designated by the trade names "Krytox” 1506, “Krytox” 1514, “Krytox” 1645, commercially available from E.I. DuPont de Nemours and Company, "Demnum” fluids, commercially available from Daikin, and "Fomblin” Y and “Fomblin” Z fluids, commercially available from Montecatini-Edison.
  • Solvents that can be used for applying the composition of this invention include mixtures of the "Freon” series, e.g., 1,1,2-trichlorotrifluoroethane, the "FC” series of perfluorinated hydrocarbons, e.g., perfluorooctane, hexafluoroxylene, and trifluorotoluene.
  • the "Freon” series e.g., 1,1,2-trichlorotrifluoroethane
  • the "FC” series of perfluorinated hydrocarbons e.g., perfluorooctane, hexafluoroxylene, and trifluorotoluene.
  • composition of this invention can be applied to a substrate to form a low energy surface liner by the following process:
  • Substrate shapes that are suitable for the composition of the present invention include sheets, fibers, and materials of other shapes.
  • Preferred substrate materials include flexible sheet materials that are used as backings for pressure-sensitive adhesive products, such as, for example, polyester, polyimide, polyamide, polyolefin, and polycarbonate films.
  • Other substrate materials that are suitable for the composition of this invention include glass, ceramic, metal, and rubber.
  • the coating techniques that are useful for applying the composition of this invention include brushing, wire-wound rod or knife coating, spraying, curtain coating, and gravure coating.
  • a primer or an adhesion-promoting coating or to treat the substrate.
  • Such treatments are described in U.S. Patent Nos. 4,567,073 and 4,614,667.
  • a substrate bearing a coating of the cured composition of the invention on one or both major surfaces thereof can then be coated with any adhesives known in the art, such as, for example, acrylic adhesives, rubber-based adhesives, and silicone-based adhesives.
  • the adhesive-coated substrate can then be wound up into a roll, if desired.
  • Flexible, pressure-sensitive adhesive-coated sheet materials are well known in the art. See, for example, U.S. Patent Re. 24,906 (acrylate), U.S. Patent Nos. 2,857,356; 2,814,601; and 2,736,721 (siloxane), and U.S. Patent No. 3,925,283 (urethane).
  • the releasability of the coatings of this invention with respect to adhesives can be measured by various methods known in the art. The method selected depends upon whether the final product is in sheet or roll form, such as a tape. Various methods for testing pressure-sensitive tapes are reported by the Pressure-Sensitive Tape Council (PSTC) in "Test Methods for Pressure-Sensitive Tapes".
  • PSTC Pressure-Sensitive Tape Council
  • a strip of tape bearing a layer of polysiloxane adhesive was pressed against the surface of a polyfluoropolyether coating under the weight of a 2.3 kg rubber roller to produce a laminate consisting of pressure-sensitive adhesive tape and a polyfluoropolyether-coated substrate.
  • the laminate is then subjected to heat aging.
  • the release value is the force required to separate the layer of adhesive from the release-coated substrate at a peel angle of 180 ° and a peel rate of 230 cm/min.
  • the adhesive was applied to a polyfluoropolyether-coated substrate by means of a knife coater or other suitable coating device, dried, and cured if required.
  • the exposed surface of the layer of adhesive was then laminated to a polyester film having a thickness of 50 micrometers. Strips having a width of 2.5 cm were cut from this laminate, and the release value was measured as described above.
  • the readhesion value of the pressure-sensitive tape was determined as follows:
  • the pressure-sensitive adhesive was applied to the surface of a clean glass plate by means of a 2.3 kg rubber roller.
  • the readhesion value is a measure of the force required to pull the tape from the glass surface at an angle of 180° at a rate of 230 cm/min.
  • the ratio by weight of polyfluoropolyether bis(triethoxysilane) to polyfluoropolyether fluid was 95:5, 90:10; 05:15, 80:20, and 70:30.
  • the polyfluoropolyether fluids used were "Krytox" 1506 and "Krytox” 1514 fluids.
  • a cure catalyst dibutyltin diacetate (2% by weight, based on total polyfluoropolyether charge), was added to each solution.
  • Release liners were made by coating the aforementioned solutions onto polyethylene terephthalate films (50 micrometers thick) by means of a #4 Mayer bar, thereby producing coatings having a nominal coating thickness of 0.5 micrometers.
  • the liners were cured for about 16 hours at about 25°C.
  • the cured liners were laminated to 2.5 cm wide strips of adhesive tape having an aggressively tacky methylsilicone pressure-sensitive adhesive ("MacDermid" MACu Tape P-3) by pressing the adhesive into contact with the liner by means of a 2.3 kg rubber roller.
  • MacDermid aggressively tacky methylsilicone pressure-sensitive adhesive
  • This example demonstrates preparation of release coatings for solvent-cast silicone adhesives.
  • Release liners were applied to PET film (50 micrometers) by means of coating with a #4 R.D.S. wire-wound rod a solution containing 6% by weight of a mixture of 83% by weight polyfluoropolyether bis( triethoxysilane) (Compound I) and 17% by weight "Krytox" 1506 fluid in a solvent containing 40% by volume 1,1,2-trichlorotrifluoroethane ("Freon” 113) and 60% by volume perfluorooctane (“FC-75”).
  • the solution also contained 4% by weight dibutyltin diacetate (based on total polyfluoropolyether charge).
  • This example demonstrates the preparation of release coatings having a high content of inert perfluoropolyether fluid.
  • This example demonstrates the effect of concentration of inert perfluoropolyether fluid on performance of release coatings with a solvent-cast peroxide cured adhesive.
  • Three coating solutions comprising 1.1% by weight mixtures of polyfluoropolyether bis(triethoxysilane) (Compound I) and "Krytox" 1514 fluid, were prepared.
  • the ratio by weight of polyfluoropolyether bis(triethoxysilane) to polyfluoropolyether fluid was 83.3:16.7, 75:25, and 67:33.
  • the solution also contained 4% by weight (based on total polyfluoropolyether charge) dibutyltin diacetate as the cure catalyst.
  • These solutions were coated onto PET film (50 micrometers) by means of a #4 R.D.S. wire-wound rod. The coatings were cured at 110°C for one minute and then allowed to stand overnight in air at room temperature.
  • Silicone adhesive (DC-7406)(33% by weight solids in toluene) with 2% by weight (based on silicone solids) initiator (“Cadox TS-50”) was applied to the release coatings by means of a knife coater (300 micrometers orifice). The adhesive was dried at 70°C for 10 minutes, cured at 150°C for five minutes, and laminated to PET film (50 micrometers). Strips of 2.5 cm width were cut for peel test measurements. Initial release, release upon aging (70°C for 72 hours) and readhesion were evaluated by the procedures described in Example 1. The results are set forth in Table IV.
  • Release coatings were prepared according to the procedures used in Example 4 from 1.1% by weight solutions of mixtures of polyfluoropolyether bis(triethoxysilane) (Compound I) and various polyfluoropolyether inert fluids. Solvent, catalyst, coating conditions, and curing conditions used were identical to those used in Example 4. The coatings were tested according to the procedures described in Examples 1 and 2. The coatings were laminated with silicone adhesives ("MacDermid" P-3 and DC-355), and initial release, release after aging, and readhesion values were measured. The results are set forth in Table V.
  • a release coating was prepared according to the procedure described in Example 5 from a 1.1% by weight solution of a mixture of polyfluoropolyether bis(triethoxysilane) (Compound I) and "Braycote” 815Z inert polyfluoropolyether fluid.
  • the weight ratio of Compound I to the inert fluid was 67:33.
  • Solvent, catalyst, coating conditions, and curing conditions were identical to those of Example 5.
  • the coating was tested with silicone adhesives ("MacDermid” P-3 and DC-355) by means of procedures described in Examples 1 and 2, and initial readhesion and readhesion after aging were measured. The results are set forth in Table VI.
  • Coating solutions containing 1.0% by weight of mixtures of polyfluoropolyether bis(triethoxysilane) (Compound I) and "Krytox" 1514 fluid were prepared.
  • the solvent consisted of 40% by volume 1,1,2-trichlorotrifluoroethane ("Freon” 113) and 60% by volume perfluorotributylamine (“FC-43”).
  • the solutions also contained 4% by weight (based on total polyfluoropolyether charge) dibutyltin diacetate.
  • These solutions were coated on polyimide film (“Kapton”)(25 micrometers) by means of a #4 R.D.S. wire-wound rod, and cured at 110°C for 10 minutes.
  • This example describes the preparation of ultraviolet radiation-cured release coating prepared from “Krytox” 1514 fluid and polyfluoropolyether diacrylate (Compound III).
  • Coating solutions consisting of 1.1% by weight of 100% polyfluoropolyether diacrylate (Compound III) and a mixture of 67% by weight Compound III and 33% by weight "Krytox” 1514 fluid in a solvent consisting of 40% by volume 1,1,2-trichlorotrifluoroethane ("Freon” 113) and 60% by volume perfluorotributylamine (“FC-43”) were prepared.
  • This example describes the preparation of ultraviolet radiation-cured release coatings with added photoinitiator.
  • This example describes preparation of release coatings based on urethane-cure chemistry.
  • a coating solution (hereinafter Solution C) was prepared by mixing, in a vial, polyfluoropolyether diol (Compound IV) (0.85 g), toluenediisocyanate (0.12 g), "Krytox”1514 fluid (0.32 g), and 1,1,2-trichlorotrifluoroethane ("Freon” 113) (20.2 g).
  • Solution D A coating solution (hereinafter Solution D) was prepared by mixing, in a vial, polyfluoropolyether diol (Compound IV) (1.13 g), toluenediisocyanate (0.16 g), and 1,1,2-trichlorotrifluoroethane ("Freon" 113) (20.2 g). After the mixture was shaken to form Solution D, dibutyltin diacetate (0.022 g) was added thereto. Solution C and Solution D were coated on PET film (50 micrometers) by means of a #4 R.D.S.
  • This example describes the use of a polyurethane substrate.
  • Solution E A coating solution (hereinafter Solution E) was prepared by mixing, in a vial, polyfluoropolyether diol (Compound IV) (0.88 g), toluenediisocyanate (0.15 g), "Krytox” 1514 fluid (0.26 g), and 1,1,2-trichlorotrifluoroethane ("Freon” 113) (20.15 g). After the mixture was shaken to form a solution, dibutyltin diacetate (0.052 g) was added.
  • Solution F A coating solution (hereinafter Solution F) was prepared in the same way from polyfluoropolyether diol (Compound IV) (1.10 g), toluenediisocyanate (0.19 g), trichlorotrifluoroethane ("Freon” 113) (20.15 g), and dibutyltin diacetate (0.052 g). These solutions were coated on "Gravel Guard” polyurethane film by means of a #4 R.D.S. wire-wound rod. The coatings were cured at 110°C for five minutes, then allowed to age overnight in air at room temperature. They were laminated to strips of silicone adhesive tape ("MacDermid" P-3), and the laminates were tested to determine initial release, release after aging, and readhesion according to the procedures described in Example 1. The results are set forth in Table XI.
  • This example describes the overcoating of inert fluid on a coating of the curable component.
  • Polyfluoropolyether bis(triethoxysilane) (Compound I) was coated onto PET film (50 micrometers) and cured in the identical manner as described in Example 1. After the coating was cured overnight at room temperature, it was overcoated with a solution of 1% by weight "Krytox" 1506 fluid in perfluorooctane ("FC-75") by means of a #4 R.D.S. wire-wound rod. After the solvent had evaporated, the composite coating was laminated to strips of silicone adhesive ("MacDermid" P-3) and the laminates were tested to determine initial release, release after aging, and readhesion by means of the procedures of Example 1. The results were as follows. Release: Initial, 0.1 N/dm; aged, 0.2 N/dm. Readhesion: Initial, 38.1 N/dm; aged, 39.4 N/dm. The control readhesion of a fresh adhesive was approximately 39 N/dm.
  • This example describes the use of crosslinkable perfluoroether polymer with pendant perfluoroether groups attached to the backbone.
  • This solution was coated on PET film (50 micrometers) by means of a #4 R.D.S. wire-wound rod, and the coating was cured at 100°C for five minutes and then allowed to stand overnight in air at room temperature.
  • the coating was tested with silicone adhesive (DC-355) according to the procedure described in Example 2. The results were as follows. Release: Initial 0.2 N/dm; aged 0.2N/dm. Readhesion: Initial 78.7 N/dm; aged 78.3 N/dm. The control readhesion of fresh adhesive was approximately 82 N/dm.

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Claims (14)

  1. Zusammensetzung, geeignet für die Herstellung einer Release-Beschichtung, umfassend 15 % ... 75 Gewichtsprozent eines Polyfluorpolyethers, enthaltend mindestens zwei reaktionsfähige Gruppen, und 25 %... 85 Gewichtsprozent eines Polyfluorpolyetheröls.
  2. Zusammensetzung nach Anspruch 1, bei welcher der inerte Polyfluorpolyether bei 25 °C eine Viskosität von 20 ... 500 mPa·s hat.
  3. Zusammensetzung nach Anspruch 1, bei welcher der inerte Polyfluorpolyether bei 25 °C eine Viskosität von 90 ... 900 mPa·s hat.
  4. Zusammensetzung nach Anspruch 1, bei welcher der mindestens zwei reaktionsfähige Gruppen enthaltende Polyfluorpolyether zum Vernetzen oder Polymerisieren oder beides in der Lage ist.
  5. Zusammensetzung nach Anspruch 4, bei welcher die reaktionsfähigen Gruppen des Polyfluorpolyethers ausgewählt werden aus der Gruppe, bestehend aus Acrylat, Hydrosilan, Silanol, Silalkoxy, Epoxy und Isocyanat.
  6. Zusammensetzung nach Anspruch 1, bei welcher das inerte Polyfluorpolyetheröl
    Figure imgb0052
     ist und worin n 13, 19 oder 26 beträgt.
  7. Zusammensetzung nach Anspruch 1, bei welcher das inerte Polyfluorpolyetheröl
    Figure imgb0053
     ist und n 25 beträgt.
  8. Zusammensetzung nach Anspruch 1, bei welcher das inerte Polyfluorpolyetheröl
    Figure imgb0054
     ist und worin sind:
    n =   16
    m =   1
    X ...   CF₃, C₂F₅, C₃F₇ oder C₄F₉.
  9. Zusammensetzung nach Anspruch 1, bei welcher der mindestens zwei reaktionsfähige Gruppen enthaltende Polyfluorpolyether
    Figure imgb0055
     ist und worin sind:
    m =   12
    n =   10
    und das inerte Polyfluorpolyetheröl
    Figure imgb0056
     ist und worin n 13 oder 19 beträgt.
  10. Zusammensetzung nach Anspruch 1, bei welcher der mindestens zwei reaktionsfähige Gruppen enthaltende Polyfluorpolyether 50 %... 75 Gewichtsprozent der Zusammensetzung ausmacht.
  11. Lösung, umfassend die Zusammensetzung nach Anspruch 1 und ein Lösemittel, ausgewählt aus der Gruppe, bestehend aus verdampfungsfähigen Fluorkohlenstoffen, Chlorfluorkohlenstoffen und Mischungen davon, wobei die Viskosität der Lösung ausreichend niedrig ist, um die Abscheidung einer dünnen, zusammenhängenden Beschichtung auf einem Substrat zu ermöglichen.
  12. Substrat, welches eines Beschichtung aufweist, die aus der Zusammensetzung nach Anspruch 11 gebildet wurde, welche Beschichtung durch Wärmeenergie oder durch aktinische Energie vernetzt wurde.
  13. Band, umfassend einen Träger, der auf einer seiner größeren Oberflächen eine Schicht aus Haftklebstoff aufweist und auf der anderen seiner größeren Oberfläche eine Release-Beschichtung, die aus der Zusammensetzung nach Anspruch 1 erzeugt wurde.
  14. Band nach Anspruch 13, bei welchem der Haftklebstoff ein Silicon-Polymer umfaßt.
EP90313595A 1989-12-14 1990-12-13 Fluorkohlenstoffhaltige Beschichtungszusammensetzung und daraus abgeleitete Produkte Expired - Lifetime EP0433070B1 (de)

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AU6669890A (en) 1991-06-20
DE69025151D1 (de) 1996-03-14
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JP3009744B2 (ja) 2000-02-14
KR0178513B1 (ko) 1999-04-01
US5306758A (en) 1994-04-26
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JPH03258863A (ja) 1991-11-19
BR9006319A (pt) 1991-09-24
EP0433070A3 (en) 1992-01-08

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